A kind of method of directly synthesizing biaryl compound without metal catalysis
A technology of metal-free catalysis and biaromatic hydrocarbons, which is applied in the preparation of organic compounds, hydrocarbons, hydrocarbons, etc., can solve the problems of poor compatibility, and achieve the effects of good compatibility, good economy and wide sources
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Embodiment 1
[0023]
[0024] N 2 Under protection, redistilled acetonitrile (2.5mL) was added to a 25ml reaction tube, then cesium fluoride 76mg (0.5mmol) was added, and then para-chlorodiphenyl sulfoxide (68mg, 0.25mmol ) and trimethylsilylphenyl trifluoromethanesulfonate (149.2 mg, 0.5 mmol), and the reaction solution was stirred at room temperature for 36 hours. During this reaction, additional cesium fluoride (38.0 mg, 0.25 mmol) and trimethylsilylphenyl triflate (74.6 mg, 0.25 mmol) were added at 12 hours and 24 hours, respectively. TLC was used to trace the reaction process, after the reaction was completed, it was concentrated by filtration and separated by column chromatography to obtain 45.2 mg of product with a yield of 81% and a purity of more than 99%. The target product is a known compound, and the obtained NMR spectrum data are consistent with the literature reports. (P. Puthiaraj, P. Suresh, and K. Pitchumani, Green. Chem. 2014, 16, 2865):
[0025] 1 H NMR (600MHz, CD...
Embodiment 2
[0027]
[0028] N 2 Under protection, redistilled acetonitrile (2.5mL) was added to a 25ml reaction tube, then cesium fluoride 76mg (0.5mmol) was added, and then para-brominated diphenylsulfoxide (60mg, 0.25mmol ) and trimethylsilylphenyl trifluoromethanesulfonate (149.2 mg, 0.5 mmol), and the reaction solution was stirred at room temperature for 36 hours. During this reaction, additional cesium fluoride (38.0 mg, 0.25 mmol) and trimethylsilylphenyl triflate (74.6 mg, 0.25 mmol) were added at 12 hours and 24 hours, respectively. TLC was used to trace the reaction process, after the reaction was completed, it was concentrated by filtration and separated by column chromatography to obtain 57.7 mg of product with a yield of 74% and a purity of more than 99%. The target product is a known compound, and the obtained NMR spectrum data are consistent with the literature reports. (P. Puthiaraj, P. Suresh, and K. Pitchumani, Green. Chem. 2014, 16, 2865):
[0029] 1 H NMR (600MHz...
Embodiment 3
[0031]
[0032] N 2 Under protection, redistilled acetonitrile (2.5mL) was added to a 25ml reaction tube, then cesium fluoride 76mg (0.5mmol) was added, and then para-OTs substituted diphenylsulfoxide (136mg, 0.25mmol ) and trimethylsilylphenyl trifluoromethanesulfonate (149.2 mg, 0.5 mmol), and the reaction solution was stirred at room temperature for 36 hours. During this reaction, additional cesium fluoride (38.0 mg, 0.25 mmol) and trimethylsilylphenyl triflate (74.6 mg, 0.25 mmol) were added at 12 hours and 24 hours, respectively. TLC was used to trace the reaction process, after the reaction was completed, it was concentrated by filtration and separated by column chromatography to obtain 65.5 mg of the product with a yield of 53% and a purity of more than 99%. The target product is a white solid with a melting point of 190–192°C.
[0033] 1 H NMR (600MHz, CDCl 3 ):δ7.73(d,J=8.3Hz,4H),7.45–7.40(m,4H),7.32(d,J=8.1Hz,4H),7.06–7.01(m,4H),2.45(s, 6H).
[0034] 13 C N...
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